# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Compound_(+/-)2 #===================================================================== _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C7 H9 N O S' _chemical_formula_sum 'C7 H9 N O S' _chemical_formula_iupac ? _chemical_formula_weight 155.21 _chemical_melting_point ? _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.0243(8) _cell_length_b 26.279(5) _cell_length_c 6.0065(10) _cell_angle_alpha 90 _cell_angle_beta 96.332(6) _cell_angle_gamma 90 _cell_volume 788.2(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1291 _cell_measurement_theta_min 3.1007 _cell_measurement_theta_max 22.6673 _cell_measurement_temperature 300.(2) _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.220 _exptl_crystal_size_mid 0.140 _exptl_crystal_size_min 0.090 _exptl_crystal_density_diffrn 1.308 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.340 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_absorpt_correction_T_min 0.84 _exptl_absorpt_correction_T_max 0.97 _exptl_special_details ; ; _diffrn_ambient_temperature 300(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'micro-focus sealed tube' _diffrn_radiation_monochromator 'doubly curved silicon crystal' _diffrn_measurement_device_type 'Bruker SMART X2S' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.3330 _diffrn_reflns_number 4846 _diffrn_reflns_av_R_equivalents 0.0350 _diffrn_reflns_av_sigmaI/netI 0.0399 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 25.12 _diffrn_reflns_theta_full 25.12 _diffrn_measured_fraction_theta_max 0.984 _diffrn_measured_fraction_theta_full 0.984 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 7 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 1374 _reflns_number_gt 1051 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0716 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_gt 0.1232 _refine_ls_wR_factor_ref 0.1484 _refine_ls_goodness_of_fit_ref 1.182 _refine_ls_restrained_S_all 1.182 _refine_ls_number_reflns 1374 _refine_ls_number_parameters 100 _refine_ls_number_restraints 2 _refine_ls_hydrogen_treatment mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0819P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.330 _refine_diff_density_min -0.381 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'Bruker Instrument Service v2009, 3, 0, 0' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Mercury 3.0 (Macrae et al, 2008)' _computing_publication_material ? _iucr_refine_instructions_details ; TITL scan_0m in P2(1)/n CELL 0.71073 5.0243 26.2794 6.0065 90.000 96.332 90.000 ZERR 4.00 0.0008 0.0047 0.0010 0.000 0.006 0.000 LATT 1 SYMM 0.5-X, 0.5+Y, 0.5-Z SFAC C H N O S UNIT 28 36 4 4 4 L.S. 10 ACTA BOND $H FMAP 2 PLAN 4 SIZE 0.090 0.140 0.220 DFIX 0.86 0.05 N9 H9A DFIX 0.86 0.05 N9 H9B EQIV $1_[ x-1/2, -y+1/2, z+1/2 ] EQIV $2_[ x+1/2, -y+1/2, z+1/2 ] HTAB N9 O8_$1 HTAB N9 O8_$2 CONF HTAB TEMP 27.000 WGHT 0.081900 FVAR 0.32255 MOLE 1 S7 5 0.628726 0.193381 0.416717 11.00000 0.02548 0.04348 = 0.04574 -0.00004 0.00644 0.00143 C1 1 0.353947 0.150453 0.341811 11.00000 0.03016 0.04019 = 0.03888 -0.00056 0.00644 0.00100 C4 1 -0.048414 0.080416 0.201697 11.00000 0.03604 0.04381 = 0.06614 -0.01220 0.00680 0.00056 C6 1 0.288137 0.112472 0.485333 11.00000 0.05034 0.04776 = 0.04536 0.00703 -0.00086 -0.00431 AFIX 43 H6 2 0.378289 0.109937 0.628678 11.00000 -1.20000 AFIX 0 C2 1 0.219618 0.153700 0.128877 11.00000 0.04413 0.05149 = 0.03688 0.00333 0.00840 -0.00093 AFIX 43 H2 2 0.263434 0.178984 0.030891 11.00000 -1.20000 AFIX 0 C5 1 0.087840 0.078365 0.414454 11.00000 0.05375 0.04263 = 0.06415 0.00661 0.00723 -0.00884 AFIX 43 H5 2 0.043094 0.053227 0.512761 11.00000 -1.20000 AFIX 0 C3 1 0.018286 0.118824 0.062353 11.00000 0.04687 0.05834 = 0.04637 -0.00949 -0.00557 -0.00038 AFIX 43 H3 2 -0.073793 0.121531 -0.080204 11.00000 -1.20000 AFIX 0 O8 4 0.572186 0.237760 0.262793 11.00000 0.03927 0.05094 = 0.05670 0.01203 0.00749 -0.00713 N9 3 0.561985 0.205304 0.672191 11.00000 0.03799 0.05475 = 0.04168 -0.00607 0.00064 -0.00275 C10 1 -0.269805 0.042899 0.125901 11.00000 0.04938 0.05936 = 0.11024 -0.02285 0.00255 -0.01226 AFIX 137 H10A 2 -0.199426 0.008912 0.135506 11.00000 -1.50000 H10B 2 -0.338953 0.050119 -0.026224 11.00000 -1.50000 H10C 2 -0.411030 0.045942 0.220492 11.00000 -1.50000 AFIX 0 H9A 2 0.691799 0.220038 0.739236 11.00000 0.05624 H9B 2 0.409064 0.221735 0.655058 11.00000 0.06904 HKLF 4 REM scan_0m in P2(1)/n REM R1 = 0.0468 for 1051 Fo > 4sig(Fo) and 0.0716 for all 1374 data REM 100 parameters refined using 2 restraints END WGHT 0.0821 0.0000 REM Highest difference peak 0.330, deepest hole -0.381, 1-sigma level 0.123 Q1 1 -0.2912 0.0251 0.2766 11.00000 0.05 0.33 Q2 1 -0.2134 0.0244 -0.0255 11.00000 0.05 0.32 Q3 1 -0.4542 0.0674 0.0751 11.00000 0.05 0.32 Q4 1 -0.2666 0.0075 0.1555 11.00000 0.05 0.28 ; loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S S7 0.62873(14) 0.19338(3) 0.41672(15) 0.0380(3) Uani d . 1 . . C C1 0.3539(6) 0.15045(12) 0.3418(6) 0.0362(7) Uani d . 1 . . C C4 -0.0484(6) 0.08042(13) 0.2017(7) 0.0486(9) Uani d . 1 . . C C6 0.2881(7) 0.11247(13) 0.4853(6) 0.0483(9) Uani d . 1 . . H H6 0.3783 0.1099 0.6287 0.058 Uiso calc R 1 . . C C2 0.2196(7) 0.15370(13) 0.1289(6) 0.0439(8) Uani d . 1 . . H H2 0.2634 0.179 0.0309 0.053 Uiso calc R 1 . . C C5 0.0878(7) 0.07836(14) 0.4145(7) 0.0535(10) Uani d . 1 . . H H5 0.0431 0.0532 0.5128 0.064 Uiso calc R 1 . . C C3 0.0183(7) 0.11882(14) 0.0624(6) 0.0513(9) Uani d . 1 . . H H3 -0.0738 0.1215 -0.0802 0.062 Uiso calc R 1 . . O O8 0.5722(4) 0.23776(9) 0.2628(4) 0.0488(7) Uani d . 1 . . N N9 0.5620(7) 0.20530(12) 0.6722(5) 0.0451(8) Uani d D 1 . . C C10 -0.2698(8) 0.04290(16) 0.1259(8) 0.0735(13) Uani d . 1 . . H H10A -0.1994 0.0089 0.1355 0.11 Uiso calc R 1 . . H H10B -0.339 0.0501 -0.0262 0.11 Uiso calc R 1 . . H H10C -0.411 0.0459 0.2205 0.11 Uiso calc R 1 . . H H9A 0.692(7) 0.2200(13) 0.739(6) 0.056(12) Uiso d D 1 . . H H9B 0.409(7) 0.2217(14) 0.655(7) 0.069(13) Uiso d D 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S7 0.0255(4) 0.0435(5) 0.0457(6) 0.0014(3) 0.0064(3) 0.0000(4) C1 0.0302(15) 0.0402(17) 0.0389(19) 0.0010(12) 0.0064(13) -0.0006(15) C4 0.0360(18) 0.044(2) 0.066(3) 0.0006(14) 0.0068(17) -0.0122(18) C6 0.050(2) 0.048(2) 0.045(2) -0.0043(15) -0.0009(16) 0.0070(17) C2 0.0441(18) 0.051(2) 0.037(2) -0.0009(15) 0.0084(15) 0.0033(16) C5 0.054(2) 0.0426(19) 0.064(3) -0.0088(16) 0.0072(18) 0.0066(18) C3 0.047(2) 0.058(2) 0.046(2) -0.0004(17) -0.0056(16) -0.0095(18) O8 0.0393(12) 0.0509(14) 0.0567(16) -0.0071(11) 0.0075(11) 0.0120(12) N9 0.0380(17) 0.0548(19) 0.0417(19) -0.0028(15) 0.0006(14) -0.0061(14) C10 0.049(2) 0.059(2) 0.110(4) -0.0123(19) 0.003(2) -0.023(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S7 O8 . 1.496(2) ? S7 N9 . 1.637(3) ? S7 C1 . 1.801(3) ? C1 C2 . 1.381(5) ? C1 C6 . 1.383(5) ? C4 C3 . 1.376(5) ? C4 C5 . 1.383(5) ? C4 C10 . 1.518(5) ? C6 C5 . 1.379(5) ? C6 H6 . 0.93 ? C2 C3 . 1.391(5) ? C2 H2 . 0.93 ? C5 H5 . 0.93 ? C3 H3 . 0.93 ? N9 H9A . 0.82(3) ? N9 H9B . 0.88(3) ? C10 H10A . 0.96 ? C10 H10B . 0.96 ? C10 H10C . 0.96 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O8 S7 N9 . . 112.68(15) ? O8 S7 C1 . . 104.23(14) ? N9 S7 C1 . . 97.09(16) ? C2 C1 C6 . . 119.7(3) ? C2 C1 S7 . . 118.4(2) ? C6 C1 S7 . . 121.7(3) ? C3 C4 C5 . . 117.5(3) ? C3 C4 C10 . . 120.9(4) ? C5 C4 C10 . . 121.6(4) ? C5 C6 C1 . . 119.5(3) ? C5 C6 H6 . . 120.2 ? C1 C6 H6 . . 120.2 ? C1 C2 C3 . . 119.4(3) ? C1 C2 H2 . . 120.3 ? C3 C2 H2 . . 120.3 ? C6 C5 C4 . . 122.0(3) ? C6 C5 H5 . . 119.0 ? C4 C5 H5 . . 119.0 ? C4 C3 C2 . . 121.8(3) ? C4 C3 H3 . . 119.1 ? C2 C3 H3 . . 119.1 ? S7 N9 H9A . . 108.(3) ? S7 N9 H9B . . 105.(3) ? H9A N9 H9B . . 117.(4) ? C4 C10 H10A . . 109.5 ? C4 C10 H10B . . 109.5 ? H10A C10 H10B . . 109.5 ? C4 C10 H10C . . 109.5 ? H10A C10 H10C . . 109.5 ? H10B C10 H10C . . 109.5 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O8 S7 C1 C2 . . . . 24.3(3) ? N9 S7 C1 C2 . . . . 139.9(3) ? O8 S7 C1 C6 . . . . -160.4(3) ? N9 S7 C1 C6 . . . . -44.8(3) ? C2 C1 C6 C5 . . . . -0.3(5) ? S7 C1 C6 C5 . . . . -175.6(3) ? C6 C1 C2 C3 . . . . 0.4(5) ? S7 C1 C2 C3 . . . . 175.9(3) ? C1 C6 C5 C4 . . . . 0.9(6) ? C3 C4 C5 C6 . . . . -1.5(6) ? C10 C4 C5 C6 . . . . -179.6(3) ? C5 C4 C3 C2 . . . . 1.7(6) ? C10 C4 C3 C2 . . . . 179.7(3) ? C1 C2 C3 C4 . . . . -1.1(5) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N9 H9B O8 4_566 0.88(3) 2.16(4) 2.981(4) 156.(4) ? N9 H9A O8 4_666 0.82(3) 2.20(3) 2.966(4) 155.(4) ? _database_code_depnum_ccdc_archive 'CCDC 939053' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Compound_(S)2 #===================================================================== _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C7 H9 N O S' _chemical_formula_sum 'C7 H9 N O S' _chemical_formula_iupac ? _chemical_formula_weight 155.21 _chemical_absolute_configuration ad _chemical_melting_point ? _space_group_crystal_system orthorhombic _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 4.9534(6) _cell_length_b 6.4415(8) _cell_length_c 24.643(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 786.29(17) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1519 _cell_measurement_theta_min 3.2689 _cell_measurement_theta_max 26.4641 _cell_measurement_temperature 296.(2) _exptl_crystal_description Rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.090 _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.341 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_absorpt_correction_T_min 0.6408 _exptl_absorpt_correction_T_max 0.7454 _exptl_special_details ; ; _diffrn_ambient_temperature 296.(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II DUO' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 4800 _diffrn_reflns_av_R_equivalents 0.0295 _diffrn_reflns_av_sigmaI/netI 0.0357 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 26.78 _diffrn_reflns_theta_full 26.78 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 1683 _reflns_number_gt 1495 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0442 _refine_ls_R_factor_gt 0.0361 _refine_ls_wR_factor_gt 0.0860 _refine_ls_wR_factor_ref 0.0896 _refine_ls_goodness_of_fit_ref 1.156 _refine_ls_restrained_S_all 1.156 _refine_ls_number_reflns 1683 _refine_ls_number_parameters 100 _refine_ls_number_restraints 1 _refine_ls_hydrogen_treatment mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0455P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.286 _refine_diff_density_min -0.163 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.03(11) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'Bruker Instrument Service v2009, 3, 0, 0' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Mercury 3.0 (Macrae et al, 2008)' _computing_publication_material ? _iucr_refine_instructions_details ; TITL mo_SEL_KE_Sulfinamide_S_EtOH_0 in P2(1)2(1)2(1) CELL 0.71073 4.9534 6.4415 24.6429 90.000 90.000 90.000 ZERR 4.00 0.0006 0.0008 0.0032 0.000 0.000 0.000 LATT -1 SYMM 0.5-X, -Y, 0.5+Z SYMM -X, 0.5+Y, 0.5-Z SYMM 0.5+X, 0.5-Y, -Z SFAC C H N O S UNIT 28 36 4 4 4 L.S. 10 ACTA BOND $H FMAP 2 PLAN 20 HTAB CONF HTAB N9 O8_$2 HTAB N9 O8_$1 EQIV $2_[ -x-1, y+1/2, -z+3/2 ] EQIV $1_[ -x, y+1/2, -z+3/2 ] DFIX 0.86 0.02 N9 H9A DFIX 0.76 0.02 N9 N9B TEMP 23.000 WGHT 0.045500 FVAR 0.31512 MOLE 1 C1 1 -0.056415 0.124789 0.850974 11.00000 0.03050 0.03876 = 0.03604 0.00380 0.00028 -0.00547 C2 1 0.047625 -0.070879 0.842866 11.00000 0.04969 0.03235 = 0.04616 0.00106 -0.00662 -0.00230 AFIX 43 H2 2 -0.011759 -0.150606 0.813755 11.00000 -1.20000 AFIX 0 C3 1 0.241200 -0.149456 0.878099 11.00000 0.04851 0.03809 = 0.05948 0.01040 0.00238 0.00387 AFIX 43 H3 2 0.310253 -0.281757 0.872130 11.00000 -1.20000 AFIX 0 C4 1 0.333255 -0.035624 0.921735 11.00000 0.03281 0.06106 = 0.04408 0.01620 0.00024 -0.00438 C5 1 0.226078 0.162519 0.929362 11.00000 0.04683 0.06415 = 0.04019 -0.00264 -0.00931 -0.00396 AFIX 43 H5 2 0.286474 0.242720 0.958300 11.00000 -1.20000 AFIX 0 C6 1 0.032263 0.242154 0.894881 11.00000 0.04134 0.04474 = 0.04592 -0.00847 -0.00235 0.00279 AFIX 43 H6 2 -0.038717 0.373757 0.900988 11.00000 -1.20000 AFIX 0 S7 5 -0.323032 0.209479 0.807228 11.00000 0.02518 0.04345 = 0.04241 -0.00025 -0.00286 -0.00470 O8 4 -0.279184 0.086763 0.756218 11.00000 0.04081 0.05145 = 0.04702 -0.00912 -0.01126 -0.00510 H9A 2 -0.076772 0.474758 0.788251 11.00000 0.04056 H9B 2 -0.357804 0.520294 0.779940 11.00000 0.05697 N9 3 -0.229881 0.452597 0.801511 11.00000 0.03338 0.03929 = 0.05550 0.00505 -0.00450 0.00230 C10 1 0.545948 -0.122505 0.959028 11.00000 0.04270 0.09162 = 0.06304 0.03156 -0.00693 -0.00226 AFIX 137 H10A 2 0.535250 -0.271312 0.959085 11.00000 -1.50000 H10B 2 0.516910 -0.071316 0.995146 11.00000 -1.50000 H10C 2 0.721273 -0.080274 0.946628 11.00000 -1.50000 HKLF 4 REM mo_SEL_KE_Sulfinamide_S_EtOH_0 in P2(1)2(1)2(1) REM R1 = 0.0361 for 1495 Fo > 4sig(Fo) and 0.0442 for all 1683 data REM 100 parameters refined using 1 restraints END WGHT 0.0477 0.0502 REM Highest difference peak 0.286, deepest hole -0.163, 1-sigma level 0.042 Q1 1 -0.1672 0.1704 0.8291 11.00000 0.05 0.29 Q2 1 -0.5008 0.2024 0.8151 11.00000 0.05 0.24 Q3 1 -0.3371 0.1674 0.7664 11.00000 0.05 0.21 Q4 1 0.1884 0.2129 0.8982 11.00000 0.05 0.18 Q5 1 -0.2767 -0.0255 0.7601 11.00000 0.05 0.16 Q6 1 -0.1395 0.0919 0.7409 11.00000 0.05 0.16 Q7 1 -0.1574 0.1558 0.7754 11.00000 0.05 0.15 Q8 1 0.0537 0.4311 0.8731 11.00000 0.05 0.15 Q9 1 -0.0840 0.0163 0.7668 11.00000 0.05 0.15 Q10 1 0.6767 -0.1920 0.9277 11.00000 0.05 0.15 Q11 1 -0.0186 0.1474 0.8869 11.00000 0.05 0.14 Q12 1 0.7037 -0.0505 0.9672 11.00000 0.05 0.14 Q13 1 0.0156 0.1823 0.8626 11.00000 0.05 0.13 Q14 1 -0.3270 0.0979 0.7317 11.00000 0.05 0.13 Q15 1 -0.1454 0.1579 0.8710 11.00000 0.05 0.13 Q16 1 0.0501 0.2040 0.9300 11.00000 0.05 0.13 Q17 1 -0.2006 0.4529 0.8472 11.00000 0.05 0.13 Q18 1 -0.3870 0.1568 0.7304 11.00000 0.05 0.12 Q19 1 0.0661 -0.1329 0.8746 11.00000 0.05 0.12 Q20 1 -0.0554 0.0044 0.8574 11.00000 0.05 0.12 ; loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C C1 -0.0564(5) 0.1248(3) 0.85097(8) 0.0351(5) Uani d . 1 . . C C2 0.0476(6) -0.0709(3) 0.84287(9) 0.0427(6) Uani d . 1 . . H H2 -0.0118 -0.1506 0.8138 0.051 Uiso calc R 1 . . C C3 0.2412(5) -0.1495(4) 0.87810(9) 0.0487(7) Uani d . 1 . . H H3 0.3103 -0.2818 0.8721 0.058 Uiso calc R 1 . . C C4 0.3333(6) -0.0356(4) 0.92174(9) 0.0460(6) Uani d . 1 . . C C5 0.2261(6) 0.1625(4) 0.92936(9) 0.0504(7) Uani d . 1 . . H H5 0.2865 0.2427 0.9583 0.06 Uiso calc R 1 . . C C6 0.0323(5) 0.2422(4) 0.89488(9) 0.0440(6) Uani d . 1 . . H H6 -0.0387 0.3738 0.901 0.053 Uiso calc R 1 . . S S7 -0.32303(12) 0.20948(9) 0.807228(19) 0.03701(17) Uani d . 1 . . O O8 -0.2792(4) 0.0868(2) 0.75622(6) 0.0464(4) Uani d . 1 . . H H9A -0.077(4) 0.475(4) 0.7883(9) 0.041(7) Uiso d D 1 . . H H9B -0.358(6) 0.520(4) 0.7799(10) 0.057(8) Uiso d . 1 . . N N9 -0.2299(4) 0.4526(3) 0.80151(9) 0.0427(5) Uani d D 1 . . C C10 0.5459(6) -0.1225(5) 0.95903(10) 0.0658(8) Uani d . 1 . . H H10A 0.5353 -0.2713 0.9591 0.099 Uiso calc R 1 . . H H10B 0.5169 -0.0713 0.9951 0.099 Uiso calc R 1 . . H H10C 0.7213 -0.0803 0.9466 0.099 Uiso calc R 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1 0.0305(12) 0.0388(11) 0.0360(10) -0.0055(10) 0.0003(9) 0.0038(9) C2 0.0497(16) 0.0324(11) 0.0462(12) -0.0023(11) -0.0066(11) 0.0011(9) C3 0.0485(18) 0.0381(12) 0.0595(13) 0.0039(11) 0.0024(11) 0.0104(10) C4 0.0328(13) 0.0611(14) 0.0441(11) -0.0044(14) 0.0002(11) 0.0162(10) C5 0.0468(17) 0.0642(17) 0.0402(11) -0.0040(13) -0.0093(10) -0.0026(10) C6 0.0413(14) 0.0447(14) 0.0459(11) 0.0028(11) -0.0023(10) -0.0085(10) S7 0.0252(3) 0.0434(3) 0.0424(3) -0.0047(3) -0.0029(2) -0.0002(2) O8 0.0408(11) 0.0514(9) 0.0470(8) -0.0051(8) -0.0113(7) -0.0091(7) N9 0.0334(12) 0.0393(10) 0.0555(12) 0.0023(9) -0.0045(9) 0.0051(9) C10 0.0427(18) 0.092(2) 0.0630(15) -0.0023(17) -0.0069(13) 0.0316(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 C2 . 1.376(3) ? C1 C6 . 1.391(3) ? C1 S7 . 1.790(2) ? C2 C3 . 1.389(3) ? C2 H2 . 0.93 ? C3 C4 . 1.379(3) ? C3 H3 . 0.93 ? C4 C5 . 1.395(4) ? C4 C10 . 1.506(4) ? C5 C6 . 1.381(3) ? C5 H5 . 0.93 ? C6 H6 . 0.93 ? S7 O8 . 1.5007(15) ? S7 N9 . 1.639(2) ? N9 H9A . 0.838(17) ? N9 H9B . 0.94(3) ? C10 H10A . 0.96 ? C10 H10B . 0.96 ? C10 H10C . 0.96 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 C1 C6 . . 119.5(2) ? C2 C1 S7 . . 117.90(17) ? C6 C1 S7 . . 122.40(18) ? C1 C2 C3 . . 120.1(2) ? C1 C2 H2 . . 120.0 ? C3 C2 H2 . . 120.0 ? C4 C3 C2 . . 121.5(2) ? C4 C3 H3 . . 119.3 ? C2 C3 H3 . . 119.3 ? C3 C4 C5 . . 117.8(2) ? C3 C4 C10 . . 120.6(2) ? C5 C4 C10 . . 121.6(2) ? C6 C5 C4 . . 121.4(2) ? C6 C5 H5 . . 119.3 ? C4 C5 H5 . . 119.3 ? C5 C6 C1 . . 119.8(2) ? C5 C6 H6 . . 120.1 ? C1 C6 H6 . . 120.1 ? O8 S7 N9 . . 112.99(10) ? O8 S7 C1 . . 103.72(10) ? N9 S7 C1 . . 97.78(11) ? S7 N9 H9A . . 116.8(19) ? S7 N9 H9B . . 107.7(17) ? H9A N9 H9B . . 108.(2) ? C4 C10 H10A . . 109.5 ? C4 C10 H10B . . 109.5 ? H10A C10 H10B . . 109.5 ? C4 C10 H10C . . 109.5 ? H10A C10 H10C . . 109.5 ? H10B C10 H10C . . 109.5 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C6 C1 C2 C3 . . . . -0.5(4) ? S7 C1 C2 C3 . . . . -175.43(19) ? C1 C2 C3 C4 . . . . 0.2(4) ? C2 C3 C4 C5 . . . . -0.2(4) ? C2 C3 C4 C10 . . . . -179.2(2) ? C3 C4 C5 C6 . . . . 0.7(4) ? C10 C4 C5 C6 . . . . 179.6(3) ? C4 C5 C6 C1 . . . . -1.0(4) ? C2 C1 C6 C5 . . . . 0.9(4) ? S7 C1 C6 C5 . . . . 175.61(19) ? C2 C1 S7 O8 . . . . -26.4(2) ? C6 C1 S7 O8 . . . . 158.84(19) ? C2 C1 S7 N9 . . . . -142.43(19) ? C6 C1 S7 N9 . . . . 42.8(2) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N9 H9B O8 3_456 0.94(3) 2.05(3) 2.947(3) 160.(2) ? N9 H9A O8 3_556 0.838(17) 2.198(17) 3.021(3) 168.(3) ? _database_code_depnum_ccdc_archive 'CCDC 939055' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Compound_1(+/-)2 #===================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 F4 I2, 4(C7 H9 N O S)' _chemical_formula_sum 'C34 H36 F4 I2 N4 O4 S4' _chemical_formula_weight 1022.71 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.1527(6) _cell_length_b 12.1505(16) _cell_length_c 16.292(2) _cell_angle_alpha 84.040(4) _cell_angle_beta 88.391(4) _cell_angle_gamma 78.975(4) _cell_volume 995.7(2) _cell_formula_units_Z 1 _cell_measurement_temperature 300(2) _cell_measurement_reflns_used 2754 _cell_measurement_theta_min 2.2268 _cell_measurement_theta_max 22.4864 _exptl_crystal_description Needle _exptl_crystal_colour 'clear colourless' _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.706 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 506 _exptl_absorpt_coefficient_mu 1.850 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6255 _exptl_absorpt_correction_T_max 0.8971 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 300.(2) _diffrn_source 'micro-focus sealed tube' _diffrn_source_type Bruker _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator 'doubly curved silicon crystal' _diffrn_measurement_device_type 'Bruker SMART X2S' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.3330 _diffrn_reflns_number 10222 _diffrn_reflns_av_R_equivalents 0.0354 _diffrn_reflns_av_sigmaI/netI 0.0458 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 25.73 _reflns_number_total 3734 _reflns_number_gt 2836 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Instrument Service v2009, 3, 0, 0' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Mercury 3.0 (Macrae et al, 2008)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _iucr_refine_instructions_details ; TITL Kevin in P-1 CELL 0.71073 5.1527 12.1505 16.2915 84.040 88.391 78.975 ZERR 1.00 0.0006 0.0016 0.0022 0.004 0.004 0.004 LATT 1 SFAC C H N O F S I UNIT 34 36 4 4 4 4 2 Omit 0 1 0 Omit 0 0 1 Omit 0 1 1 L.S. 20 ACTA BOND $H FMAP 2 PLAN 5 HTAB N15 O24_$1 HTAB N15 S23_$1 HTAB N15 O24_$2 HTAB N25 O14_$3 HTAB N25 O14_$4 EQIV $1_[ x+1, y-1, z+1 ] EQIV $2_[ x, y-1, z+1 ] EQIV $3_[ x-1, y+1, z-1 ] EQIV $4_[ x, y+1, z-1 ] HTAB HTAB CONF SIZE 0.060 0.110 0.280 DFIX 0.86 0.02 N15 H15A DFIX 0.86 0.02 N15 H15B TEMP 27.000 WGHT 0.036600 FVAR 0.16942 MOLE 1 C1 1 0.375136 0.560237 0.564984 11.00000 0.05187 0.03610 = 0.04095 -0.00581 0.00200 -0.00046 C2 1 0.549757 0.603578 0.511327 11.00000 0.05903 0.03140 = 0.06011 -0.01181 0.00821 -0.00812 C3 1 0.671837 0.545382 0.448566 11.00000 0.05816 0.04134 = 0.05422 -0.00231 0.01919 -0.00812 I4 7 0.195213 0.647896 0.661396 11.00000 0.06190 0.04755 = 0.04375 -0.01093 0.00445 0.00329 F5 5 0.601525 0.706672 0.519461 11.00000 0.10684 0.04877 = 0.09289 -0.03039 0.03895 -0.03697 F6 5 0.843377 0.592786 0.398922 11.00000 0.11906 0.05844 = 0.09606 -0.02074 0.06032 -0.03406 C7 1 0.664199 -0.028122 0.727011 11.00000 0.03337 0.04499 = 0.03194 -0.00314 0.00090 -0.00573 C8 1 0.589535 -0.088133 0.667946 11.00000 0.04980 0.04267 = 0.04567 -0.01183 -0.00442 -0.00032 AFIX 43 H8 2 0.674438 -0.162078 0.663575 11.00000 -1.20000 AFIX 0 C9 1 0.383070 -0.036620 0.614025 11.00000 0.05702 0.05357 = 0.03972 -0.01198 -0.00999 -0.01099 AFIX 43 H9 2 0.332590 -0.077182 0.573833 11.00000 -1.20000 AFIX 0 C10 1 0.254450 0.072446 0.619543 11.00000 0.03799 0.04811 = 0.03478 0.00417 -0.00345 -0.01069 C11 1 0.335580 0.130593 0.679417 11.00000 0.05688 0.04060 = 0.04694 -0.00611 -0.01025 0.00028 AFIX 43 H11 2 0.251761 0.204686 0.683780 11.00000 -1.20000 AFIX 0 C12 1 0.538209 0.081714 0.733153 11.00000 0.05243 0.04359 = 0.04404 -0.01198 -0.00926 -0.00332 AFIX 43 H12 2 0.589094 0.122561 0.773094 11.00000 -1.20000 AFIX 0 S13 6 0.946616 -0.090916 0.789685 11.00000 0.03313 0.05006 = 0.03833 -0.00405 -0.00061 -0.00304 O14 4 0.953537 -0.216244 0.794064 11.00000 0.04701 0.04112 = 0.04557 -0.00598 -0.00044 0.00376 H15A 2 0.685065 -0.052687 0.892023 11.00000 0.05193 H15B 2 0.964615 -0.046700 0.912358 11.00000 0.07934 N15 3 0.837968 -0.037783 0.875235 11.00000 0.04358 0.05228 = 0.04215 -0.00754 -0.00879 -0.00344 C16 1 0.028839 0.126905 0.562748 11.00000 0.04956 0.05896 = 0.04967 0.00396 -0.01523 -0.00943 AFIX 137 H16A 2 0.089908 0.127665 0.506513 11.00000 -1.50000 H16B 2 -0.035295 0.202802 0.575440 11.00000 -1.50000 H16C 2 -0.111394 0.084837 0.570216 11.00000 -1.50000 AFIX 0 C17 1 0.652458 0.715224 0.035134 11.00000 0.03433 0.04974 = 0.03855 -0.00230 -0.00013 -0.00123 C18 1 0.741405 0.793812 0.075854 11.00000 0.04638 0.04594 = 0.04561 -0.00964 -0.00192 0.00517 AFIX 43 H18 2 0.671945 0.870099 0.063859 11.00000 -1.20000 AFIX 0 C19 1 0.934678 0.758836 0.134736 11.00000 0.04863 0.05651 = 0.04976 -0.00978 -0.00582 -0.00693 AFIX 43 H19 2 0.995486 0.812706 0.161667 11.00000 -1.20000 AFIX 0 C20 1 1.040364 0.646923 0.154910 11.00000 0.03884 0.07020 = 0.03685 0.00060 0.00215 -0.00147 C21 1 0.947089 0.568840 0.113766 11.00000 0.05999 0.04543 = 0.05581 0.00441 -0.00602 0.01014 AFIX 43 H21 2 1.014968 0.492591 0.126743 11.00000 -1.20000 AFIX 0 C22 1 0.754457 0.601179 0.053478 11.00000 0.05894 0.05009 = 0.05630 -0.00785 -0.00323 -0.00916 AFIX 43 H22 2 0.694949 0.547543 0.025940 11.00000 -1.20000 AFIX 0 MOLE 2 S23 6 0.377573 0.759970 -0.034012 11.00000 0.03516 0.06061 = 0.04686 -0.00231 -0.00166 -0.00686 MOLE 1 O24 4 0.357693 0.885500 -0.049667 11.00000 0.04161 0.05410 = 0.05916 -0.00406 -0.00878 0.00335 H25A 2 0.393938 0.701666 -0.151625 11.00000 0.06417 H25B 2 0.655752 0.713186 -0.135377 11.00000 0.05906 N25 3 0.507493 0.694406 -0.113643 11.00000 0.04976 0.06202 = 0.04912 -0.00975 -0.00763 -0.01103 C26 1 1.251866 0.608445 0.220732 11.00000 0.05356 0.11022 = 0.04950 0.00542 -0.00799 -0.00060 AFIX 137 H26A 2 1.221437 0.540169 0.251393 11.00000 -1.50000 H26B 2 1.244313 0.665878 0.257462 11.00000 -1.50000 H26C 2 1.423070 0.595049 0.194801 11.00000 -1.50000 HKLF 4 REM Kevin in P-1 REM R1 = 0.0328 for 2836 Fo > 4sig(Fo) and 0.0516 for all 3734 data REM 253 parameters refined using 2 restraints END WGHT 0.0366 0.0000 REM Highest difference peak 0.369, deepest hole -0.471, 1-sigma level 0.096 Q1 1 0.6002 0.9395 -0.0078 11.00000 0.05 0.37 Q2 1 1.0479 0.6562 -0.0429 11.00000 0.05 0.33 Q3 1 0.5454 0.5990 0.4612 11.00000 0.05 0.33 Q4 1 0.6386 0.5438 0.6351 11.00000 0.05 0.31 Q5 1 0.9227 0.9379 0.0309 11.00000 0.05 0.29 ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0366P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3734 _refine_ls_number_parameters 253 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0516 _refine_ls_R_factor_gt 0.0328 _refine_ls_wR_factor_ref 0.0754 _refine_ls_wR_factor_gt 0.0678 _refine_ls_goodness_of_fit_ref 0.971 _refine_ls_restrained_S_all 0.971 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3751(7) 0.5602(3) 0.5650(2) 0.0439(9) Uani 1 1 d . . . C2 C 0.5498(8) 0.6036(3) 0.5113(2) 0.0499(10) Uani 1 1 d . . . C3 C 0.6718(8) 0.5454(3) 0.4486(2) 0.0520(10) Uani 1 1 d . . . I4 I 0.19521(5) 0.64790(2) 0.661396(15) 0.05252(11) Uani 1 1 d . . . F5 F 0.6015(5) 0.70667(19) 0.51946(16) 0.0790(8) Uani 1 1 d . . . F6 F 0.8434(6) 0.5928(2) 0.39892(17) 0.0891(9) Uani 1 1 d . . . C7 C 0.6642(6) -0.0281(3) 0.7270(2) 0.0371(8) Uani 1 1 d . . . C8 C 0.5895(7) -0.0881(3) 0.6679(2) 0.0466(9) Uani 1 1 d . . . H8 H 0.6744 -0.1621 0.6636 0.056 Uiso 1 1 calc R . . C9 C 0.3831(7) -0.0366(3) 0.6140(2) 0.0493(9) Uani 1 1 d . . . H9 H 0.3326 -0.0772 0.5738 0.059 Uiso 1 1 calc R . . C10 C 0.2544(6) 0.0724(3) 0.6195(2) 0.0405(8) Uani 1 1 d . . . C11 C 0.3356(7) 0.1306(3) 0.6794(2) 0.0491(9) Uani 1 1 d . . . H11 H 0.2518 0.2047 0.6838 0.059 Uiso 1 1 calc R . . C12 C 0.5382(7) 0.0817(3) 0.7332(2) 0.0467(9) Uani 1 1 d . . . H12 H 0.5891 0.1226 0.7731 0.056 Uiso 1 1 calc R . . S13 S 0.94662(16) -0.09092(8) 0.78968(5) 0.0412(2) Uani 1 1 d . . . O14 O 0.9535(4) -0.2162(2) 0.79406(15) 0.0461(6) Uani 1 1 d . . . H15A H 0.685(5) -0.053(3) 0.892(2) 0.052(12) Uiso 1 1 d D . . H15B H 0.965(6) -0.047(3) 0.912(2) 0.079(15) Uiso 1 1 d D . . N15 N 0.8380(7) -0.0378(3) 0.8752(2) 0.0464(8) Uani 1 1 d D . . C16 C 0.0288(7) 0.1269(3) 0.5627(2) 0.0532(10) Uani 1 1 d . . . H16A H 0.0899 0.1277 0.5065 0.080 Uiso 1 1 calc R . . H16B H -0.0353 0.2028 0.5754 0.080 Uiso 1 1 calc R . . H16C H -0.1114 0.0848 0.5702 0.080 Uiso 1 1 calc R . . C17 C 0.6525(6) 0.7152(3) 0.0351(2) 0.0419(9) Uani 1 1 d . . . C18 C 0.7414(7) 0.7938(3) 0.0759(2) 0.0474(9) Uani 1 1 d . . . H18 H 0.6719 0.8701 0.0639 0.057 Uiso 1 1 calc R . . C19 C 0.9347(7) 0.7588(3) 0.1347(2) 0.0516(10) Uani 1 1 d . . . H19 H 0.9955 0.8127 0.1617 0.062 Uiso 1 1 calc R . . C20 C 1.0404(7) 0.6469(4) 0.1549(2) 0.0503(10) Uani 1 1 d . . . C21 C 0.9471(8) 0.5688(3) 0.1138(2) 0.0570(11) Uani 1 1 d . . . H21 H 1.0150 0.4926 0.1267 0.068 Uiso 1 1 calc R . . C22 C 0.7545(8) 0.6012(3) 0.0535(2) 0.0550(10) Uani 1 1 d . . . H22 H 0.6949 0.5475 0.0259 0.066 Uiso 1 1 calc R . . S23 S 0.37757(17) 0.75997(9) -0.03401(6) 0.0480(2) Uani 1 1 d . . . O24 O 0.3577(4) 0.8855(2) -0.04967(16) 0.0532(7) Uani 1 1 d . . . H25A H 0.394(8) 0.702(3) -0.152(2) 0.064(14) Uiso 1 1 d . . . H25B H 0.656(8) 0.713(3) -0.135(2) 0.059(13) Uiso 1 1 d . . . N25 N 0.5075(8) 0.6944(3) -0.1136(2) 0.0531(9) Uani 1 1 d . . . C26 C 1.2519(8) 0.6084(4) 0.2207(3) 0.0739(14) Uani 1 1 d . . . H26A H 1.2214 0.5402 0.2514 0.111 Uiso 1 1 calc R . . H26B H 1.2443 0.6659 0.2575 0.111 Uiso 1 1 calc R . . H26C H 1.4231 0.5950 0.1948 0.111 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.052(2) 0.036(2) 0.041(2) -0.0058(16) 0.0020(17) -0.0005(17) C2 0.059(2) 0.031(2) 0.060(3) -0.0118(18) 0.008(2) -0.0081(18) C3 0.058(2) 0.041(2) 0.054(2) -0.0023(19) 0.019(2) -0.0081(19) I4 0.06190(19) 0.04755(17) 0.04375(16) -0.01093(11) 0.00445(12) 0.00329(12) F5 0.1068(19) 0.0488(14) 0.0929(19) -0.0304(13) 0.0389(16) -0.0370(14) F6 0.119(2) 0.0584(16) 0.096(2) -0.0207(14) 0.0603(17) -0.0341(15) C7 0.0334(18) 0.045(2) 0.0319(18) -0.0031(15) 0.0009(15) -0.0057(16) C8 0.050(2) 0.043(2) 0.046(2) -0.0118(18) -0.0044(18) -0.0003(17) C9 0.057(2) 0.054(3) 0.040(2) -0.0120(18) -0.0100(18) -0.011(2) C10 0.0380(19) 0.048(2) 0.0348(19) 0.0042(16) -0.0034(16) -0.0107(17) C11 0.057(2) 0.041(2) 0.047(2) -0.0061(18) -0.0103(19) 0.0003(18) C12 0.052(2) 0.044(2) 0.044(2) -0.0120(17) -0.0093(18) -0.0033(18) S13 0.0331(5) 0.0501(6) 0.0383(5) -0.0041(4) -0.0006(4) -0.0030(4) O14 0.0470(14) 0.0411(15) 0.0456(15) -0.0060(12) -0.0004(12) 0.0038(12) N15 0.044(2) 0.052(2) 0.0422(19) -0.0075(15) -0.0088(17) -0.0034(16) C16 0.050(2) 0.059(3) 0.050(2) 0.004(2) -0.0152(19) -0.0094(19) C17 0.0343(19) 0.050(2) 0.039(2) -0.0023(17) -0.0001(16) -0.0012(17) C18 0.046(2) 0.046(2) 0.046(2) -0.0096(18) -0.0019(18) 0.0052(18) C19 0.049(2) 0.057(3) 0.050(2) -0.010(2) -0.0058(19) -0.0069(19) C20 0.039(2) 0.070(3) 0.037(2) 0.0006(19) 0.0021(17) -0.0015(19) C21 0.060(3) 0.045(2) 0.056(3) 0.004(2) -0.006(2) 0.010(2) C22 0.059(2) 0.050(3) 0.056(3) -0.008(2) -0.003(2) -0.009(2) S23 0.0352(5) 0.0606(7) 0.0469(6) -0.0023(5) -0.0017(4) -0.0069(4) O24 0.0416(14) 0.0541(17) 0.0592(17) -0.0041(13) -0.0088(13) 0.0034(12) N25 0.050(2) 0.062(2) 0.049(2) -0.0098(17) -0.0076(19) -0.0110(18) C26 0.054(3) 0.110(4) 0.050(3) 0.005(3) -0.008(2) -0.001(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.376(5) . ? C1 C3 1.391(5) 2_666 ? C1 I4 2.085(3) . ? C2 F5 1.350(4) . ? C2 C3 1.373(5) . ? C3 F6 1.351(4) . ? C3 C1 1.391(5) 2_666 ? C7 C8 1.371(4) . ? C7 C12 1.380(5) . ? C7 S13 1.800(3) . ? C8 C9 1.407(5) . ? C8 H8 0.9300 . ? C9 C10 1.374(5) . ? C9 H9 0.9300 . ? C10 C11 1.380(5) . ? C10 C16 1.511(4) . ? C11 C12 1.384(5) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? S13 O14 1.511(3) . ? S13 N15 1.636(3) . ? N15 H15A 0.872(18) . ? N15 H15B 0.886(19) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C18 1.370(5) . ? C17 C22 1.389(5) . ? C17 S23 1.800(3) . ? C18 C19 1.378(5) . ? C18 H18 0.9300 . ? C19 C20 1.374(5) . ? C19 H19 0.9300 . ? C20 C21 1.380(5) . ? C20 C26 1.524(5) . ? C21 C22 1.389(5) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? S23 O24 1.504(3) . ? S23 N25 1.652(4) . ? N25 H25A 0.85(4) . ? N25 H25B 0.89(4) . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C3 116.1(3) . 2_666 ? C2 C1 I4 121.6(3) . . ? C3 C1 I4 122.3(3) 2_666 . ? F5 C2 C3 118.6(3) . . ? F5 C2 C1 119.6(3) . . ? C3 C2 C1 121.8(3) . . ? F6 C3 C2 118.5(3) . . ? F6 C3 C1 119.4(3) . 2_666 ? C2 C3 C1 122.1(3) . 2_666 ? C8 C7 C12 120.2(3) . . ? C8 C7 S13 118.7(3) . . ? C12 C7 S13 120.9(3) . . ? C7 C8 C9 119.3(3) . . ? C7 C8 H8 120.4 . . ? C9 C8 H8 120.4 . . ? C10 C9 C8 121.3(3) . . ? C10 C9 H9 119.3 . . ? C8 C9 H9 119.3 . . ? C9 C10 C11 117.9(3) . . ? C9 C10 C16 121.3(3) . . ? C11 C10 C16 120.8(3) . . ? C10 C11 C12 121.8(3) . . ? C10 C11 H11 119.1 . . ? C12 C11 H11 119.1 . . ? C7 C12 C11 119.5(3) . . ? C7 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? O14 S13 N15 112.64(16) . . ? O14 S13 C7 104.80(15) . . ? N15 S13 C7 97.34(16) . . ? S13 N15 H15A 114(3) . . ? S13 N15 H15B 112(3) . . ? H15A N15 H15B 118(4) . . ? C10 C16 H16A 109.5 . . ? C10 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C10 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 C22 120.3(3) . . ? C18 C17 S23 119.2(3) . . ? C22 C17 S23 120.1(3) . . ? C17 C18 C19 119.4(4) . . ? C17 C18 H18 120.3 . . ? C19 C18 H18 120.3 . . ? C20 C19 C18 122.1(4) . . ? C20 C19 H19 119.0 . . ? C18 C19 H19 119.0 . . ? C19 C20 C21 117.7(4) . . ? C19 C20 C26 122.0(4) . . ? C21 C20 C26 120.3(4) . . ? C20 C21 C22 121.7(4) . . ? C20 C21 H21 119.1 . . ? C22 C21 H21 119.1 . . ? C21 C22 C17 118.7(4) . . ? C21 C22 H22 120.7 . . ? C17 C22 H22 120.7 . . ? O24 S23 N25 111.92(17) . . ? O24 S23 C17 104.08(16) . . ? N25 S23 C17 98.04(18) . . ? S23 N25 H25A 110(3) . . ? S23 N25 H25B 117(3) . . ? H25A N25 H25B 109(4) . . ? C20 C26 H26A 109.5 . . ? C20 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C20 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 C1 C2 F5 178.7(3) 2_666 . . . ? I4 C1 C2 F5 -1.8(5) . . . . ? C3 C1 C2 C3 -0.5(6) 2_666 . . . ? I4 C1 C2 C3 179.0(3) . . . . ? F5 C2 C3 F6 1.6(6) . . . . ? C1 C2 C3 F6 -179.2(4) . . . . ? F5 C2 C3 C1 -178.7(4) . . . 2_666 ? C1 C2 C3 C1 0.6(7) . . . 2_666 ? C12 C7 C8 C9 -0.2(5) . . . . ? S13 C7 C8 C9 -174.8(3) . . . . ? C7 C8 C9 C10 -0.2(6) . . . . ? C8 C9 C10 C11 0.5(5) . . . . ? C8 C9 C10 C16 -178.7(3) . . . . ? C9 C10 C11 C12 -0.5(6) . . . . ? C16 C10 C11 C12 178.7(3) . . . . ? C8 C7 C12 C11 0.2(5) . . . . ? S13 C7 C12 C11 174.7(3) . . . . ? C10 C11 C12 C7 0.2(6) . . . . ? C8 C7 S13 O14 -29.2(3) . . . . ? C12 C7 S13 O14 156.3(3) . . . . ? C8 C7 S13 N15 -145.0(3) . . . . ? C12 C7 S13 N15 40.5(3) . . . . ? C22 C17 C18 C19 0.5(5) . . . . ? S23 C17 C18 C19 173.8(3) . . . . ? C17 C18 C19 C20 -0.7(6) . . . . ? C18 C19 C20 C21 0.2(6) . . . . ? C18 C19 C20 C26 -179.3(3) . . . . ? C19 C20 C21 C22 0.5(6) . . . . ? C26 C20 C21 C22 180.0(4) . . . . ? C20 C21 C22 C17 -0.6(6) . . . . ? C18 C17 C22 C21 0.1(6) . . . . ? S23 C17 C22 C21 -173.1(3) . . . . ? C18 C17 S23 O24 16.4(3) . . . . ? C22 C17 S23 O24 -170.4(3) . . . . ? C18 C17 S23 N25 131.5(3) . . . . ? C22 C17 S23 N25 -55.3(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N15 H15B O24 0.886(19) 2.12(3) 2.921(4) 150(4) 1_646 N15 H15B S23 0.886(19) 2.93(3) 3.580(3) 132(3) 1_646 N15 H15A O24 0.872(18) 2.14(2) 2.994(4) 168(3) 1_546 N25 H25A O14 0.85(4) 2.45(4) 3.210(4) 150(4) 1_464 N25 H25B O14 0.89(4) 2.15(4) 3.024(5) 167(3) 1_564 _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.73 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.369 _refine_diff_density_min -0.471 _refine_diff_density_rms 0.096 _database_code_depnum_ccdc_archive 'CCDC 939056' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Compound_1(S)2 #===================================================================== _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C6 F4 I2, C7 H9 N O S ' _chemical_formula_sum 'C13 H9 F4 I2 N O S' _chemical_formula_iupac ? _chemical_formula_weight 557.07 _chemical_absolute_configuration ad _chemical_melting_point ? _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'P 1 21 1' _space_group_name_Hall 'P 2yb' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.867(4) _cell_length_b 6.102(3) _cell_length_c 15.553(7) _cell_angle_alpha 90 _cell_angle_beta 103.913(11) _cell_angle_gamma 90 _cell_volume 816.8(6) _cell_formula_units_Z 2 _cell_measurement_reflns_used 4411 _cell_measurement_theta_min 2.4258 _cell_measurement_theta_max 27.1031 _cell_measurement_temperature 130.(2) _exptl_crystal_description Needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.240 _exptl_crystal_size_mid 0.110 _exptl_crystal_size_min 0.090 _exptl_crystal_density_diffrn 2.265 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 4.017 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_absorpt_correction_T_min 0.4817 _exptl_absorpt_correction_T_max 0.7455 _exptl_special_details ; ; _diffrn_ambient_temperature 130.(2) _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'Bruker 3kW tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II DUO' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 10316 _diffrn_reflns_av_R_equivalents 0.0489 _diffrn_reflns_av_sigmaI/netI 0.0520 _diffrn_reflns_theta_min 1.35 _diffrn_reflns_theta_max 27.32 _diffrn_reflns_theta_full 27.32 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measured_fraction_theta_full 0.993 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 3649 _reflns_number_gt 3402 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0355 _refine_ls_R_factor_gt 0.0320 _refine_ls_wR_factor_gt 0.0752 _refine_ls_wR_factor_ref 0.0769 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.035 _refine_ls_number_reflns 3649 _refine_ls_number_parameters 202 _refine_ls_number_restraints 1 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0377P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 1.669 _refine_diff_density_min -1.342 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.04(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection ? _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Mercury 3.0 (Macrae et al, 2008)' _computing_publication_material ? _iucr_refine_instructions_details ; TITL mo_SEL_KE_3_Co_010_0m in P2(1) CELL 0.71073 8.8672 6.1020 15.5528 90.000 103.913 90.000 ZERR 2.00 0.0038 0.0026 0.0066 0.000 0.011 0.000 LATT -1 SYMM -x, y+1/2, -z SFAC C H N O F S I UNIT 26 18 2 2 8 2 4 L.S. 20 ACTA BOND $H FMAP 2 PLAN 50 CONF HTAB N21 O20_$1 EQIV $1_[ -x+1, y+1/2, -z+2 ] RTAB Dist I11 O20_$1 WGHT 0.037700 0.000000 FVAR 0.130220 TEMP -143.200 C1 1 0.250031 0.112350 0.330087 11.000000 0.014760 = 0.024010 0.017190 0.002230 0.000720 0.000120 C2 1 0.191634 0.041044 0.243542 11.000000 0.017560 = 0.016230 0.027330 0.001450 0.005870 0.000570 C3 1 0.084808 0.167878 0.185030 11.000000 0.016770 = 0.029070 0.011520 -0.002500 0.004050 -0.002330 C4 1 0.035328 0.364727 0.209649 11.000000 0.011810 = 0.024730 0.021030 -0.000030 -0.000420 0.000520 C5 1 0.093672 0.433022 0.295131 11.000000 0.020680 = 0.018510 0.023700 -0.000410 0.003090 0.003140 C6 1 0.199215 0.310986 0.354679 11.000000 0.016500 = 0.023180 0.019660 -0.001880 -0.001300 -0.003620 I7 7 0.407830 -0.074529 0.419628 11.000000 0.021050 = 0.029890 0.025180 0.004010 -0.003180 0.003690 F8 5 0.237160 -0.147744 0.216357 11.000000 0.029330 = 0.023830 0.026880 -0.003500 0.002790 0.007850 F9 5 0.032244 0.092496 0.101867 11.000000 0.030700 = 0.029090 0.019190 -0.003100 -0.000930 -0.001000 I10 7 -0.124479 0.554359 0.117928 11.000000 0.016680 = 0.021400 0.023590 0.002830 -0.001790 0.000250 F11 5 0.045574 0.624287 0.323301 11.000000 0.032230 = 0.022970 0.028470 -0.008790 0.000930 0.005980 F12 5 0.248784 0.381631 0.436892 11.000000 0.032180 = 0.029300 0.019570 -0.007670 -0.003240 0.002550 C13 1 0.511607 0.850353 0.830804 11.000000 0.018150 = 0.023720 0.031380 -0.006650 0.010590 -0.000750 C14 1 0.440436 0.648495 0.829321 11.000000 0.039290 = 0.019040 0.038660 -0.003610 0.010400 0.001070 AFIX 43 H14 2 0.470421 0.549685 0.877622 11.000000 -1.200000 AFIX 0 C15 1 0.321409 0.592531 0.753811 11.000000 0.035610 = 0.029360 0.046920 -0.010840 0.016610 -0.002590 AFIX 43 H15 2 0.269894 0.455456 0.751845 11.000000 -1.200000 AFIX 0 C16 1 0.280074 0.733824 0.683843 11.000000 0.020730 = 0.051880 0.035920 -0.018500 0.009930 -0.001030 C17 1 0.355344 0.932312 0.687667 11.000000 0.028810 = 0.051660 0.018400 0.000510 0.004960 -0.005310 AFIX 43 H17 2 0.326593 1.031382 0.639374 11.000000 -1.200000 AFIX 0 C18 1 0.472274 0.990341 0.760639 11.000000 0.025020 = 0.038570 0.025140 -0.000970 0.004640 -0.006780 AFIX 43 H18 2 0.524574 1.126566 0.761740 11.000000 -1.200000 AFIX 0 S19 6 0.670839 0.907796 0.924282 11.000000 0.019040 = 0.032310 0.028060 0.001550 0.005320 0.003170 O20 4 0.641923 0.763325 0.995158 11.000000 0.023680 = 0.038640 0.039560 0.014250 0.002270 0.005400 N21 3 0.630329 1.163651 0.938972 11.000000 0.030410 = 0.029490 0.022360 0.000330 -0.002940 -0.005700 C22 1 0.157415 0.672894 0.601415 11.000000 0.037550 = 0.077950 0.040290 -0.030180 0.006020 -0.004530 AFIX 137 H22A 2 0.100475 0.804698 0.576194 11.000000 -1.500000 H22B 2 0.084993 0.567214 0.616883 11.000000 -1.500000 H22C 2 0.207414 0.607347 0.557837 11.000000 -1.500000 AFIX 3 H21A 2 0.536307 1.174014 0.927702 11.000000 0.095010 H21B 2 0.677745 1.202836 0.987100 11.000000 0.121490 AFIX HKLF 4 1 1 0 0 0 1 0 0 0 1 END Q1 1 -0.106200 0.560000 0.177700 11.000000 0.050000 1.670000 Q2 1 0.385300 -0.074500 0.361500 11.000000 0.050000 1.590000 Q3 1 0.419000 -0.069000 0.479500 11.000000 0.050000 1.500000 Q4 1 -0.144600 0.547200 0.059500 11.000000 0.050000 1.370000 Q5 1 -0.186300 0.670300 0.157800 11.000000 0.050000 0.650000 Q6 1 0.418100 0.061800 0.537200 11.000000 0.050000 0.590000 Q7 1 0.463900 -0.187800 0.402800 11.000000 0.050000 0.490000 Q8 1 -0.186800 0.478800 0.128200 11.000000 0.050000 0.490000 Q9 1 0.353000 -0.012200 0.423200 11.000000 0.050000 0.470000 Q10 1 0.371100 0.073600 0.462800 11.000000 0.050000 0.470000 Q11 1 0.716700 0.053000 0.742800 11.000000 0.050000 0.450000 Q12 1 0.247800 -0.130300 0.144100 11.000000 0.050000 0.450000 Q13 1 -0.004800 0.917100 0.283500 11.000000 0.050000 0.440000 Q14 1 0.084300 0.394800 0.080700 11.000000 0.050000 0.440000 Q15 1 0.156700 0.420100 0.804000 11.000000 0.050000 0.430000 Q16 1 -0.091400 0.413200 0.099400 11.000000 0.050000 0.430000 Q17 1 0.384100 0.280900 0.618000 11.000000 0.050000 0.420000 Q18 1 0.125600 0.237300 0.059000 11.000000 0.050000 0.420000 Q19 1 0.469200 0.029500 0.403400 11.000000 0.050000 0.410000 Q20 1 0.094600 0.679700 0.081700 11.000000 0.050000 0.410000 Q21 1 0.079600 0.504500 0.758100 11.000000 0.050000 0.390000 Q22 1 0.401800 -0.345400 0.378200 11.000000 0.050000 0.390000 Q23 1 0.551800 1.230500 0.944900 11.000000 0.050000 0.390000 Q24 1 0.219900 0.083400 0.453400 11.000000 0.050000 0.380000 Q25 1 0.086700 0.169900 0.157800 11.000000 0.050000 0.380000 Q26 1 -0.021700 0.430600 0.184500 11.000000 0.050000 0.370000 Q27 1 0.110100 0.536500 0.701800 11.000000 0.050000 0.370000 Q28 1 0.342700 -0.169200 0.441300 11.000000 0.050000 0.370000 Q29 1 0.801200 1.248700 0.898900 11.000000 0.050000 0.360000 Q30 1 0.288800 0.716700 0.570900 11.000000 0.050000 0.360000 Q31 1 0.243600 0.590600 0.479000 11.000000 0.050000 0.360000 Q32 1 0.465500 0.885200 0.982100 11.000000 0.050000 0.360000 Q33 1 0.205100 0.911000 0.478200 11.000000 0.050000 0.360000 Q34 1 0.406400 1.215800 0.856900 11.000000 0.050000 0.360000 Q35 1 0.587700 0.071100 0.439200 11.000000 0.050000 0.360000 Q36 1 0.246600 0.950800 0.773100 11.000000 0.050000 0.350000 Q37 1 0.485100 0.722200 0.723500 11.000000 0.050000 0.350000 Q38 1 0.012700 0.280200 0.044100 11.000000 0.050000 0.350000 Q39 1 0.179500 0.556300 0.781400 11.000000 0.050000 0.350000 Q40 1 0.199700 0.050200 0.314200 11.000000 0.050000 0.350000 Q41 1 0.605700 0.923000 1.059800 11.000000 0.050000 0.350000 Q42 1 0.900900 0.888100 0.982000 11.000000 0.050000 0.340000 Q43 1 0.191300 0.748200 0.556700 11.000000 0.050000 0.340000 Q44 1 0.004700 -0.042700 0.001100 11.000000 0.050000 0.340000 Q45 1 0.054800 0.645000 0.387000 11.000000 0.050000 0.340000 Q46 1 0.226300 0.152200 0.774600 11.000000 0.050000 0.340000 Q47 1 0.108200 0.740000 0.324600 11.000000 0.050000 0.340000 Q48 1 0.097500 0.412900 0.739300 11.000000 0.050000 0.340000 Q49 1 0.679800 0.892200 0.991500 11.000000 0.050000 0.340000 Q50 1 0.059500 0.548400 0.046300 11.000000 0.050000 0.340000 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM mo_SEL_KE_3_Co_010_0m in P2(1) REM R1= 0.0320 for 3402 Fo > 4sig(Fo) and 0.0355 for all 3649 data REM 202 parameters refined using 1 restraints ; loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C C1 0.2500(7) 0.1124(9) 0.3301(4) 0.0192(13) Uani d . 1 . . C C2 0.1916(6) 0.0410(13) 0.2435(4) 0.0203(12) Uani d . 1 . . C C3 0.0848(7) 0.1679(11) 0.1850(4) 0.0190(12) Uani d . 1 . . C C4 0.0353(7) 0.3647(10) 0.2096(4) 0.0199(14) Uani d . 1 . . C C5 0.0937(7) 0.4330(12) 0.2951(4) 0.0213(12) Uani d . 1 . . C C6 0.1992(7) 0.3110(10) 0.3547(4) 0.0207(13) Uani d . 1 . . I I7 0.40783(4) -0.07453(6) 0.41963(3) 0.02686(11) Uani d . 1 . . F F8 0.2372(4) -0.1477(6) 0.2164(2) 0.0274(8) Uani d . 1 . . F F9 0.0322(4) 0.0925(6) 0.1019(2) 0.0275(9) Uani d . 1 . . I I10 -0.12448(4) 0.55436(6) 0.11793(2) 0.02169(10) Uani d . 1 . . F F11 0.0456(4) 0.6243(6) 0.3233(3) 0.0290(9) Uani d . 1 . . F F12 0.2488(4) 0.3816(6) 0.4369(2) 0.0286(9) Uani d . 1 . . C C13 0.5116(7) 0.8504(11) 0.8308(5) 0.0236(14) Uani d . 1 . . C C14 0.4404(8) 0.6485(11) 0.8293(5) 0.0322(15) Uani d . 1 . . H H14 0.4704 0.5497 0.8776 0.039 Uiso calc R 1 . . C C15 0.3214(8) 0.5925(12) 0.7538(5) 0.0362(18) Uani d . 1 . . H H15 0.2699 0.4555 0.7518 0.043 Uiso calc R 1 . . C C16 0.2801(7) 0.7338(13) 0.6838(5) 0.0356(18) Uani d . 1 . . C C17 0.3553(7) 0.9323(16) 0.6877(4) 0.0331(15) Uani d . 1 . . H H17 0.3266 1.0314 0.6394 0.04 Uiso calc R 1 . . C C18 0.4723(8) 0.9903(11) 0.7606(4) 0.0298(16) Uani d . 1 . . H H18 0.5246 1.1266 0.7617 0.036 Uiso calc R 1 . . S S19 0.67084(17) 0.9078(3) 0.92428(11) 0.0265(3) Uani d . 1 . . O O20 0.6419(5) 0.7633(9) 0.9952(3) 0.0349(11) Uani d . 1 . . N N21 0.6303(7) 1.1637(10) 0.9390(4) 0.0290(12) Uani d . 1 . . C C22 0.1574(9) 0.6729(19) 0.6014(5) 0.052(2) Uani d . 1 . . H H22A 0.1005 0.8047 0.5762 0.079 Uiso calc R 1 . . H H22B 0.085 0.5672 0.6169 0.079 Uiso calc R 1 . . H H22C 0.2074 0.6073 0.5578 0.079 Uiso calc R 1 . . H H21A 0.5363 1.174 0.9277 0.10(4) Uiso d R 1 . . H H21B 0.6777 1.2028 0.9871 0.12(5) Uiso d R 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1 0.015(3) 0.024(3) 0.017(3) 0.000(2) 0.001(2) 0.002(2) C2 0.018(3) 0.016(3) 0.027(3) 0.001(3) 0.006(2) 0.001(3) C3 0.017(3) 0.029(3) 0.012(3) -0.002(3) 0.004(2) -0.003(3) C4 0.012(3) 0.025(4) 0.021(3) 0.001(2) 0.000(2) 0.000(2) C5 0.021(3) 0.019(3) 0.024(3) 0.003(3) 0.003(2) 0.000(3) C6 0.016(3) 0.023(3) 0.020(3) -0.004(3) -0.001(2) -0.002(3) I7 0.02105(19) 0.0299(2) 0.0252(2) 0.00369(18) -0.00318(16) 0.00401(19) F8 0.0293(19) 0.0238(19) 0.027(2) 0.0079(15) 0.0028(17) -0.0035(16) F9 0.0307(18) 0.029(2) 0.0192(18) -0.0010(16) -0.0009(16) -0.0031(16) I10 0.01668(17) 0.02140(17) 0.0236(2) 0.00025(16) -0.00179(14) 0.00283(17) F11 0.032(2) 0.0230(19) 0.028(2) 0.0060(15) 0.0009(17) -0.0088(16) F12 0.032(2) 0.029(2) 0.0196(18) 0.0025(16) -0.0032(16) -0.0077(16) C13 0.018(3) 0.024(3) 0.031(4) -0.001(2) 0.011(3) -0.007(3) C14 0.039(4) 0.019(3) 0.039(4) 0.001(3) 0.010(3) -0.004(3) C15 0.036(4) 0.029(4) 0.047(4) -0.003(3) 0.017(4) -0.011(3) C16 0.021(3) 0.052(5) 0.036(4) -0.001(3) 0.010(3) -0.019(4) C17 0.029(3) 0.052(4) 0.018(3) -0.005(4) 0.005(3) 0.001(4) C18 0.025(3) 0.039(4) 0.025(3) -0.007(3) 0.005(3) -0.001(3) S19 0.0190(7) 0.0323(8) 0.0281(8) 0.0032(7) 0.0053(6) 0.0015(8) O20 0.024(2) 0.039(3) 0.040(3) 0.005(2) 0.002(2) 0.014(2) N21 0.030(3) 0.029(3) 0.022(3) -0.006(3) -0.003(3) 0.000(2) C22 0.038(4) 0.078(6) 0.040(5) -0.005(5) 0.006(4) -0.030(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 C6 . 1.379(9) ? C1 C2 . 1.391(9) ? C1 I7 . 2.064(6) ? C2 F8 . 1.323(8) ? C2 C3 . 1.382(9) ? C3 F9 . 1.346(7) ? C3 C4 . 1.365(9) ? C4 C5 . 1.370(9) ? C4 I10 . 2.100(6) ? C5 F11 . 1.351(7) ? C5 C6 . 1.368(8) ? C6 F12 . 1.320(7) ? C13 C18 . 1.364(10) ? C13 C14 . 1.382(10) ? C13 S19 . 1.801(7) ? C14 C15 . 1.419(10) ? C14 H14 . 0.95 ? C15 C16 . 1.367(11) ? C15 H15 . 0.95 ? C16 C17 . 1.377(12) ? C16 C22 . 1.515(10) ? C17 C18 . 1.387(9) ? C17 H17 . 0.95 ? C18 H18 . 0.95 ? S19 O20 . 1.481(5) ? S19 N21 . 1.630(7) ? N21 H21A . 0.8121 ? N21 H21B . 0.8018 ? C22 H22A . 0.98 ? C22 H22B . 0.98 ? C22 H22C . 0.98 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C6 C1 C2 . . 118.2(6) ? C6 C1 I7 . . 120.8(5) ? C2 C1 I7 . . 121.0(5) ? F8 C2 C3 . . 119.4(5) ? F8 C2 C1 . . 120.7(6) ? C3 C2 C1 . . 119.9(6) ? F9 C3 C4 . . 120.7(6) ? F9 C3 C2 . . 117.7(6) ? C4 C3 C2 . . 121.6(6) ? C3 C4 C5 . . 117.9(6) ? C3 C4 I10 . . 120.3(5) ? C5 C4 I10 . . 121.8(5) ? F11 C5 C6 . . 117.9(5) ? F11 C5 C4 . . 120.1(5) ? C6 C5 C4 . . 121.9(6) ? F12 C6 C5 . . 119.5(6) ? F12 C6 C1 . . 120.0(6) ? C5 C6 C1 . . 120.4(6) ? C18 C13 C14 . . 121.1(7) ? C18 C13 S19 . . 121.6(5) ? C14 C13 S19 . . 117.0(6) ? C13 C14 C15 . . 118.3(7) ? C13 C14 H14 . . 120.8 ? C15 C14 H14 . . 120.8 ? C16 C15 C14 . . 120.7(7) ? C16 C15 H15 . . 119.6 ? C14 C15 H15 . . 119.6 ? C15 C16 C17 . . 119.1(6) ? C15 C16 C22 . . 121.3(8) ? C17 C16 C22 . . 119.6(8) ? C16 C17 C18 . . 121.3(7) ? C16 C17 H17 . . 119.4 ? C18 C17 H17 . . 119.4 ? C13 C18 C17 . . 119.5(7) ? C13 C18 H18 . . 120.3 ? C17 C18 H18 . . 120.3 ? O20 S19 N21 . . 112.5(3) ? O20 S19 C13 . . 104.0(3) ? N21 S19 C13 . . 98.2(3) ? S19 N21 H21A . . 107.1 ? S19 N21 H21B . . 109.4 ? H21A N21 H21B . . 117.3 ? C16 C22 H22A . . 109.5 ? C16 C22 H22B . . 109.5 ? H22A C22 H22B . . 109.5 ? C16 C22 H22C . . 109.5 ? H22A C22 H22C . . 109.5 ? H22B C22 H22C . . 109.5 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C6 C1 C2 F8 . . . . 179.6(5) ? I7 C1 C2 F8 . . . . -0.6(8) ? C6 C1 C2 C3 . . . . -0.4(9) ? I7 C1 C2 C3 . . . . 179.3(4) ? F8 C2 C3 F9 . . . . -0.4(8) ? C1 C2 C3 F9 . . . . 179.7(5) ? F8 C2 C3 C4 . . . . -179.4(5) ? C1 C2 C3 C4 . . . . 0.7(9) ? F9 C3 C4 C5 . . . . -179.7(6) ? C2 C3 C4 C5 . . . . -0.7(8) ? F9 C3 C4 I10 . . . . 0.0(8) ? C2 C3 C4 I10 . . . . 179.0(5) ? C3 C4 C5 F11 . . . . -178.5(5) ? I10 C4 C5 F11 . . . . 1.8(8) ? C3 C4 C5 C6 . . . . 0.5(9) ? I10 C4 C5 C6 . . . . -179.2(4) ? F11 C5 C6 F12 . . . . 0.7(9) ? C4 C5 C6 F12 . . . . -178.3(6) ? F11 C5 C6 C1 . . . . 178.7(5) ? C4 C5 C6 C1 . . . . -0.3(10) ? C2 C1 C6 F12 . . . . 178.2(5) ? I7 C1 C6 F12 . . . . -1.5(8) ? C2 C1 C6 C5 . . . . 0.3(9) ? I7 C1 C6 C5 . . . . -179.5(5) ? C18 C13 C14 C15 . . . . -1.9(10) ? S19 C13 C14 C15 . . . . -175.9(5) ? C13 C14 C15 C16 . . . . 1.0(10) ? C14 C15 C16 C17 . . . . -0.2(10) ? C14 C15 C16 C22 . . . . 177.7(6) ? C15 C16 C17 C18 . . . . 0.4(11) ? C22 C16 C17 C18 . . . . -177.6(7) ? C14 C13 C18 C17 . . . . 2.1(10) ? S19 C13 C18 C17 . . . . 175.8(5) ? C16 C17 C18 C13 . . . . -1.3(11) ? C18 C13 S19 O20 . . . . 161.7(6) ? C14 C13 S19 O20 . . . . -24.3(6) ? C18 C13 S19 N21 . . . . 46.0(6) ? C14 C13 S19 N21 . . . . -140.0(5) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N21 H21A O20 2_657 0.81 2.27 2.905(8) 135.6 ? #===END _database_code_depnum_ccdc_archive 'CCDC 939058'